


Caught in the Act

by SGC



Category: Original Work
Genre: Blackmail, Crossdressing, F/M, Humiliation, Mistress, Public Humiliation, S&M, sissy
Language: English
Status: In-Progress
Published: 2017-05-31
Updated: 2017-05-31
Packaged: 2018-11-07 06:27:44
Rating: Explicit
Warnings: Rape/Non-Con
Chapters: 1
Words: 2,999
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11053218
Author URL: https://archiveofourown.org/users/SGC/pseuds/SGC
Summary: A man is caught cross-dressing in public and get's more than he bargained for.





	Caught in the Act

I walked through the gardens, sweating for two reasons. The first reason is that it was hot out. The day had decided to trick me again, freezing cold in the morning, boiling hot through the day. The second reason is that underneath my jeans and t-shirt, I was wearing a sports bra and a pink thong and I was sure someone would notice. I could feel the thong rubbing between my cheeks as I walked past the families and lovers relaxing on the grass. Surely someone could see the outline of the bra through my shirt. But through my anxiety burnt a stronger emotion. Pleasure. I felt the conflict within me. The wish to be discovered and the horror of being discovered. I worked my way deeper into the gardens and sat beneath a tree, alone for the most part. My pants bulged as the sheer, pink material rubbed against my cock. Feeling the naughtiness rise up in me, I grabbed the back of my thong and pulled it up over the top of my jeans. The way I was sitting meant my shirt didn't cover my lower back fully and the bright pink thong would be visible to anyone who looked. I shivered despite the heat and felt the need to touch myself. I rubbed myself a bit through my jeans and stifled a moan as I reached the edge in seconds. I pulled my hand away and looked around nervously. Still alone, mostly. My hands worked their way up into my shirt, seemingly by themselves and started rubbing my nipples through the sports bra. I bit my lip and fought the urge to touch myself some more. 

I took my hands out of my shirt, face red and almost had a heart attack as I felt a touch on my arm. I spun around and saw a young woman dressed in sportswear, smiling at me. She had a look in her eye that made me nervous. "C-can I help you?" I stammered, subtly trying to pull the back of my shirt down. "Are you having fun?" She said, laughter in her voice. "Wh-what do you...?" She cut me off by reaching down the back of my jeans and pulling my thong up. Hard. I yelped as the string dug into me and felt my dick stiffen involuntarily against the fabric. "What's this? Hmm?" She said, giving my panties another yank.   
"Ah... It's a thong!" I stammered. She let go and stepped around in front of me.   
"And why is a boy like you wearing a nice, pink thong?" She asked. Smirking. She loomed over me, her face close to mine.  
"I-I... It turns me on..." I whispered, mortified. She laughed and looked down at my crotch.   
"Show me." She said commandingly.   
"Wh-what?"   
"Pull down your jeans and show me, I wanna see just how turned on you are." She said.   
My heart pounded but she'd caught me. I had no choice. "Hurry up."   
I slowly unbuttoned and unzipped my jeans, my cock in plain view, bulging against the see-through pink material. Before I could do anything she stepped up and pulled my jeans down to my knees, exposing me completely. She stared at my panties for a few seconds as I looked around making sure no-one else was around. She smiled and said "Wow, it's so small! I see why you wear panties. You're like a girl. You even shaved!" I blushed but my traitorous dick leaked in my panties, clearly visible to the woman. She laughed again. "Aww are you that turned on by getting caught like this?" Before I could react she stepped back and her phone flew up, taking a picture. I gasped and covered myself with my hands, way too late. She tapped on her phone for a few seconds before turning it to face me. 

There was a picture of me, face bright red with my jeans pulled around my knees and my tiny cock pressing against my pink thong. My face was clear as day. I stepped towards her and she stepped back out of reach. "Ah ah. She said smugly. None of that, I've already sent the picture to myself so you couldn't delete it even if you wanted to." I stood there with my heart beating, not saying a word.  
"Good, so you understand." She said, grinning again. "You're mine now. Do everything I say and I might delete this picture before someone sees it..."  
I didn't answer, I couldn't.  
"What do you say?" She said, her tone sharpening.   
"Y-yes! Okay!". I stammered.  
"Yes, what?" She said mockingly.   
I paused for a second. "Y-yes, Mistress?"  
"Good girl." She patted me on the head. "Now pull up your pants and follow me." She started walking off and I struggled to pull my jeans back up and followed her, still blushing. When I caught up to her she reached behind me and pulled my thong up above my jeans again without a word. I bit my lip and kept walking, that photo burning in my mind. She led me deeper into the park and eventually she led me off to the side, into a small clearing surrounded by bushes. She turned to face me and said one word. "Strip."  
I licked my lips and pulled my shoes off. My skin crawling as I felt the open air around me. I pulled off my shoes and socks and then pulled off my shirt, exposing my bra. "You can keep that and the panties on." She interjected.   
I pulled down my jeans and slipped them all the way off this time, shivering. It didn't feel so hot now.  
She walked around me, inspecting me. "You even shaved your legs, I'm impressed." She ran a hand gently along my thigh as she passed. I shivered.   
"Fold up your clothes and give them to me". She said, silhouetted against the sun which was low on the horizon. I did as she asked and handed her the clothes. She put them in her bag. "Now, kneel in front of me."   
I kneeled at her feet, shivering. She slapped me across the face. "What do you say?"   
"Y-yes Mistress!" I cried. My face burned from more than just the blow.   
She took her shoes off and stood in front of me. "Now kiss my feet, slut. And make sure you do it properly."  
I leant forwards on my hands and knees and started kissing her feet, burning with shame. I could feel the breeze against my ass and the thong between my cheeks raised up in the air. As I kissed her feet she looked down at me, smiling. "Imagine if your friends could see you now hmm? Does anyone else know what a slut you are?"   
I shook my head and mouthed around her toes "No Mistress."   
"I thought not." I heard the sound of a shutter going off and looked up to see she'd taken another picture of me. "Be a good girl if you want to keep it that way." My face burned as I made out with her toes, desperately trying to do a good job. She kept me going a while longer before telling me to stop. I went to lift my face up but she stood on my head, pressing my face into the ground. "Keep your face there and raise that ass as high as you can." She commanded. I lifted my butt up as far as I could. "Good girl." She said again, taking her foot off my head. She walked around behind me and stroked the wet spot on my panties. I let out a girly moan and she giggled, pulling her hand away. She walked back around the front and squatted next to my face. She offered her fingers to me. Blushing, I opened my mouth and she shoved her fingers in. "You made a mess, slut. Lick it all off."   
"Mss Msstrss", I choked around her fingers, slurping up my precum. She took her time, fucking my throat with her finger before pulling them out and walking around behind me again. I gasped drool leaking down my chin and my eyes watering. With one swift movement she pulled my panties aside, revealing my cock and ass to the sky. She gently slid her fingers down the length of my cock, laughing as I moaned again. When she reached the base she kept going, down my balls and ending up gently stroking my ass. I let out another involuntary moan. "Ooooh, yeah, you like it there, don't you slut?" She crooned, circling my ass with her wet fingers. 

I let out another moan in answer. "Do you want me to put it in? Do you want me to fuck your sissy ass?"   
My cock twitched and I heard myself saying "Mnnn Yes Mistress"...  
She smiled and started stroking slower, fingering the hole but just not putting it in. "I think you can ask better than that, I want to hear you beg."  
I squirmed against her fingers wanting nothing more than to feel them inside of me. "Pleeease... Fuck my slutty ass Mistress... Mnnnnn..."  
"Good Girl", she said and slipped her middle finger all the way in, stroking the inside in a way that felt like heaven. I was moaning truly now, forgetting that anyone could be nearby. "Th-thank you M-Mistressss" I moaned, moving my hips to the rhythm of her fingers. I felt my cock swinging limply between my legs, dripping precum onto the grass. She sped up and my mind started to get hazy. It just felt so good. After a while she slipped in a second finger and my mind nearly shut off completely. My eyes widened and I felt a rush of pleasure flow through me. I cried out as a pathetic spurt of cum shot out of my cock splattering against the grass. Mistress pulled her fingers out of me and I collapsed, panting, my face still on the ground. I gasped in pain as she grabbed me by the hair and pulled my head up to look at her. "Did I say you could cum?"  
My heart sank. "No Mistress."   
"That's right." She said. She pulled me by the hair over to where my puddle of cum was. She pressed my face into the puddle and started rubbing against it. "Clean it up, slut. And then I'm going to punish you for this."   
I tried my best to slurp the cum off the grass. My face burned with shame again. Not just from this but from cumming just from my ass being fingered. She kept a firm hold on my hair as the taste of cum filled my mouth. After a while she told me to stop and kneel. I did what she said and she looked down at me again. She pulled out her phone and snapped another picture. She showed me and I saw a picture of me kneeling, face covered in cum and dirt. I blushed, a now common occurence, and hung my head.   
She handed me my shirt and said "Put this on slut." I did as she told me gratefully and waited. She pulled out a tube of lipstick. "Hold still", she said and applied it to my lips. Then she used it to write something on both my cheeks.   
"Now keep your mouth open wide and don't close it until, I say so or there'll be hell to pay"

She picked up her bag with the rest of my clothes in it and walked out of the clearing. "I'll be waiting for you at the park entrance!" She called over her shoulder and walked away laughing.   
"W-wait!" I called after her but she was already gone. Dark was truly falling now and I was alone in the clearing.   
I pulled my shirt down over my exposed cock, feeling it lift up at the back leaving my ass and the pink thong fully exposed. I opened my mouth wide, and slowly left the clearing. I reached the path and stopped, listening. I couldn't hear anyone but the park couldn't be completely empty this early. I shivered, and not because of the cold. A string of drool leaked out of my open mouth and onto my chest. I stepped out onto the path, feeling more exposed than ever in the dim light. I stood there for a few seconds like a deer in headlights before starting the long walk towards the entrance, ears straining. There was a crack of leaves and I heard muffled voices from further ahead so I ducked off the path, blood pounding, and crouched in the darkness, shaking. A couple walked past holding hands but neither of them glanced in my direction. Against all odds I felt myself getting hard again. Was this really turning me on? 

I stepped back onto the path and kept walking, my mouth aching from keeping it open for so long. There was a corner up ahead which I approached nervously. It sounded clear. I walked around the corner and kept going steadily. I was getting close now. I reached the edge of the heavy forestry and looked out upon the park entrance. It was a great square of park benches and roses and small shrubbery. Worse yet, it was very well lit and there were a few people walking around. Right across the square I could see the woman. She was right near the front entrance, right across that open space. This was my punishment. I felt like my face was a shining beacon as I stepped out into the open. The square was pretty clear now and most people were heading for the exit. A few people saw me for sure though. I kept my eyes fixed on the woman but I could feel them watching me and heard them whispering. I heard some girls giggling too which made me blush harder. How must I look? Face covered in cum and dirt, god knows what on my face in lipstick and trying to cover my tiny pink thong with a too short t-shirt? I marched straight for the woman and she looked up and smiled. I finally reached her and stopped in front of her, breathing heavily, struggling to keep my mouth open. She raised her phone and took another picture, turning it to show me. I saw what was written on my face. "WHORE". My open mouth with my overdrawn cock-suckers lips made the "O". So that's why she made me keep my mouth open. 

She tapped the bench next to her. "Sit Down." She commanded.   
I sat down without thinking, pulling my shirt over my panties.   
She tsked me. "Put your feet up on the bench, spread your legs and pull that shirt up."  
I looked at her.   
"Do it, or I send this picture to everyone you know."   
I bit my lip and did as she asked, again wishing I'd worn less see-through panties. I shivered as my cock was once again bared for anyone to see my shame.   
"Good girl. Keep that mouth open. Now I'm starting a timer for 5 minutes. At the end of that you can get dressed. If anyone sees you, I want you to look at them and make eye contact."  
"Y-yes Mistress." I choked. 

Those long five minutes passed in silence between us. Five people total saw me like that and I remember all of their faces. I'm sure they remember mine too. Most of them were middle aged men. Most of them glanced at me and looked away quickly, going on there way. One man though, stopped and looked me up and down. He stared at my cock and I blushed, staring back at him, aware my Mistress was watching me. After a few seconds he winked at me and walked out. 

"Time's up. Close your mouth." Said the woman gently. She held out my jeans. I took them and put them on, shaking in my hurry. "Th-thank you Mistress."   
She smiled and hugged me. "You did good. I'm proud of you honey."  
"Thank you Mistress". I replied, feeling a weird sense of relief as she hugged me.   
"What did you learn?" She asked.   
"D-don't cum without permission?"  
"Good girl. You can go now." She kissed me on the forehead.   
"Wait, but what about the pictures?" I said, recovering a little.   
"Don't worry, I'll delete it." She said with a grin.  
"Thank you... Mistress."  
I turned and walked out of the park with a sigh feeling the adrenaline rush slowly leave me. I felt a little sad, to my surprise. Was that not really what I wanted this whole time? I shook myself and kept walking. Of course not. As I walked towards the train station I felt my phone buzz in my pocket. I pulled it out and gasped when I opened the message. The contact was saved as "Mistress" and the text read: "I deleted that picture, but I didn't say anything about these three. Stand by for further instructions. Byeee. <3" and attached were the three other pictures of me. The one with my face down and my ass in the air, the one of me kneeling and covered in cum and the last one she took of me with my "WHORE" face writing. Before I could react, another message came through. "P.S set one of those pictures as your phone background. I'll know if you don't obey. Xx" Damn it, she must have got my number from my phone. It was in my jeans that whole time. I bit my lip and found I was feeling a little happy. My life was definitely about to get interesting if nothing else. I noticed people kept looking at me as I walked past and with a start I remembered I still had WHORE written on my face! I rubbed it off, heatedly as best I could and made my long way home.


End file.
